Known methods for separating and analyzing an enantiomer mixture of compounds containing an asymmetric carbon atom through liquid chromatography by using an optically active compound-grafted packing material include a ligand exchange method reported by V. Davankov et al. wherein an optically active proline-grafted packing material is employed (cf. J. Chromatogr., 141, 313 (1977)); a charge transfer complex method reported by F. Mikes et al. wherein a .pi.-electron-lacking, optically active compound-grafted packing material is employed (cf. J. Chromatogr., 122, 205 (1976)); a method for separation of N-acylated amino acid esters or N-acylated dipeptide esters using an optically active N-acylated amino acid-grafted packing material as reported by Hara et al. (cf. J. Liquid Chromatogr., 2, 883 (1979) and J. Chromatogr., 186, 543 (1979)); and a method for separation of 3,5-dinitrobenzoylated amino acids, amines, hydroxy acids or sulfoxides using an optically active 1-(9-anthryl)-trifluoroethanol-grafted packing material as well as a method for separation of aromatic alcohols using a 3,5-dinitrobenzoylated, optically active phenylglycine-grafted packing material as reported by W. Pirkle et al. (cf. J. Org. Chem., 44, 1957 (1979)).
However there is no effective packing material for directly separating and analyzing an enantiomer mixture of, for example, an ester or an alcohol, except those reported by W. Pirkle et al. Further there are a number of enantiomer mixtures which cannot be separated even by the Pirkle's method. In addition, the separation of an enantiomer mixture by this method would be sometimes insufficient. Thus the Pirkle's method can be applied to only limited cases. Accordingly it has been keenly required to develop a novel packing material of an improved performance to thereby overcome the above problems.